title: Protecting group free synthesis of 6-substituted naphthols and binols.
abstract: A straightforward route for the preparation of 6-substituted naphthols and 6,6'-disubstituted binols (binol = 2,2'-dihydroxy-1,1'-binaphthyl) is presented. The synthesis has been accomplished by a one-step procedure starting from 6-bromo derivatives via direct lithiation with n-BuLi, followed by the addition of several electrophiles. This C-C functionalization has been successfully achieved with iodomethane, 3-methoxybenzaldehyde, benzophenone, methyl-2-methylbenzoate, methylbenzoate, dimethyl carbonate, ethyl 2-chloro-2-oxoacetate, and 2,2-dimethyloxirane (E). This reactivity offers a useful protecting group free synthetic protocol, toward chiral disubstituted 6,6'-binols with configuration retention of the binol moiety.
authors.affiliation: Dipartimento di Chimica Organica, Università di Pavia, V.le Taramelli 10, 27100 Pavia, Italy. danielaverga@gmail.com
authors.forename: Daniela
authors.initials: D
authors.lastname: Verga
authors.forename: Claudia
authors.initials: C
authors.lastname: Percivalle
authors.forename: Filippo
authors.initials: F
authors.lastname: Doria
authors.forename: Alessio
authors.initials: A
authors.lastname: Porta
authors.forename: Mauro
authors.initials: M
authors.lastname: Freccero